Holiday rentals in Jacksonville

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Top-rated holiday rentals in Jacksonville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guest suite in Jacksonville

4.84 out of 5 average rating, 269 reviews

Claudia's Retreat Sanctuary

Retreat here on my 6 acres of madrone forest with pastoral views, 2 meditation labyrinths- yet only 3 miles to the quaint, historic town of Jacksonville, Oregon, home of Britt Festival, 35 minutes to Ashland and 1.5 hours to Mt. Shasta or Crater Lake. This guest suite in the lower level of my house and has uphill access to the hot tub by the garden. Book a Sacred Sound bath session with Tibetan and crystal bowls & Paiste gongs for $70 during your stay. Massage chair available too. Simply divine!

19–26 Jul

$108 SGD per night

Guest favourite

Guest suite in Jacksonville

4.97 out of 5 average rating, 357 reviews

Spring Savings-Private 2-Bedroom Suite in J-ville

Welcome to the Nathe Nest where you’ll enjoy a little piece of heaven in the quaint historic town of Jacksonville. The "Suite" is cozy, convenient, and your "Welcome Baskets" are filled with plush towels and each closet has two robes to make you feel right at home. Owner lives in the main part of the house with an adjoining door to the Sunroom only, it has locks and blinds for privacy. Very rarely do you hear anything from the owners side. EXTRA GUEST FEE over 2 GUESTS $30 PER PERSON/PER NIGHT.

12–19 Sep

$182 SGD per night

Guest favourite

Guest suite in Jacksonville

4.91 out of 5 average rating, 189 reviews

2-bedroom suite, only 1 mile to Jacksonville

Family and Senior friendly In Jacksonville, 1 mile to town. Cozy, quiet, scenic, isolated in the hills. Modern home with central A/C and heat, good cell signal, ceiling fans . Master Bedroom, key pad entry, King bed, fine sheets, TV with Amazon Prime, Bathroom, large towels, large jetted tub, double sink. Kitchenette with fridge-freezer, microwave, George Foreman grille, double burner, coffee pot, toaster, and blender. Adjacent bedroom Queen bed and desk with power strip. Private entry door.

26 Sep – 3 Oct

$182 SGD per night

Guest favourite

Home in Jacksonville

4.99 out of 5 average rating, 249 reviews

Britt Bungalow in the Heart of Jacksonville

An elegant single level newly built (2019) private 2 bed/2 bath cottage with 17' ceilings, #1 Dreamcloud mattress in Master, substantial natural light & family friendly fenced in front & PRIVATE backyard. EV Charger. Less than 2-blocks from dining & the lovely Britt Festival Concert venue. Enjoy historic tours on trolly out the front door. FAMILY: Park & walkable to grocery store. FITNESS: Local gym near by and hiking trails. RELAX: Free standing bath tub, bench swing on porch, & fireplace

20–27 Jan

$379 SGD per night

Superhost

Cottage in Jacksonville

4.9 out of 5 average rating, 175 reviews

Farm Cottage on River - Applegate Wine Trail

Recently repainted and deep cleaned, cottage on a 5-acre, Applegate River farm near vineyards. This is a cozy cottage on "Red Barn Farm.” Enjoy a mini farm-stay experience with goats & chickens along the Applegate Valley Wine Trail. Walk to Red Lily Vineyards! Enjoy the private firepit with complimentary s’mores kit or walk down to the river and breath. We are 15 minutes from the historic gold-rush town of Jacksonville, home of the Britt Summer Music Festival. Wine Country Farm Stay dot come.

25 Aug – 1 Sep

$167 SGD per night

Guest favourite

Cottage in Central Point

4.98 out of 5 average rating, 390 reviews

Country Garden Cottage

Newly remodeled Garden Cottage with living area/kitchenette, bedroom, and bathroom. Cottage has high ceilings, ceramic tile floors, quartz countertop, cherry wood cabinets and new mini-split heater/air conditioner. It is bordered on two sides by a garden common area with seating, fountain, and a grape vine covered pergola. New Roku TV installed. Conveniently located: * 5 min to I-5 * 10 min to airport * 3 min to Central Point * 10 min to Medford * 5 min to Jacksonville * 25 min to Ashland

4–11 Oct

$133 SGD per night

Guest favourite

Treehouse in Jacksonville

4.98 out of 5 average rating, 186 reviews

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

14–21 Sep

$287 SGD per night

Guest favourite

Guest suite in Jacksonville

4.84 out of 5 average rating, 217 reviews

My Little Tuscany: vineyard view, deck & hot tub

This is a scenic stop between PDX and SF and its own destination. One guest says " Her home has a magic of its own." Simple, elegant, and a great base for wine-tasters, paraglider, or roadtrippers. If a house surrounded by nature, vineyards, paraglider pilots, creativity and occasional other travelers sounds interesting, you'll love it here. As a local tourism coordinator, I can direct you to the top attractions. Note: this is a self-contained unit but attached to the main house!

15–22 Nov

$120 SGD per night

Guest favourite

Guest suite in Medford

4.96 out of 5 average rating, 125 reviews

Vineyard Views from 2 Bdrm Suite on the Farm

The guesthouse on our little farm overlooks the vineyard and the fields beyond. We are in the perfect spot to easily access many of the wonderful things Southern Oregon has to offer. Explore wineries, including our own, hiking trails, the Britt festival, and more! This is a new space with lots of amenities, including an outdoor grill, kitchenette with fridge and hot plate, and full-size sleeper-sofa. Pack & play and other baby/child amenities are available upon request.

20–27 May

$202 SGD per night

Guest favourite

Guest house in Jacksonville

4.97 out of 5 average rating, 133 reviews

Valhalla Cabin, King Bed, Hiking, close to Britt

Tranquility & hiking. 128 AC of wooded acreage to hike on. The flowers bloom in the spring! Come and see! We are located about 20 min from The Britt in Jacksonville. Check out their venue and list of performers! ***This is a NO SMOKING IN OR OUT of the unit/property, This cabin is NOT suitable for children, No animals allowed EXCEPT for service dogs. When there is snow, 4-wheel vehicles are advised***

11–18 Jul

$162 SGD per night

Guest favourite

Guest house in Jacksonville

4.98 out of 5 average rating, 154 reviews

Starthistle Cottage in Applegate wine country

Rural cottage in the beautiful Applegate Valley. Peaceful with beautiful views of the landscape and wildlife. Closest lodging to Woodrat Mountain launch for paragliders & hang gliders. Nestled in the heart of the Applegate Wine Trail and the Southern Oregon Lavender Trail. Close to historical Jacksonville for the Britt Festival. Easy access to Applegate Lake and surrounding hiking trails.

9–16 Nov

$146 SGD per night

Guest favourite

Guest house in Medford

4.95 out of 5 average rating, 152 reviews

Cottage with jetted tub and fine linens

Nestled in rich farmland just north of historic Jacksonville and Britt Gardens, this cottage is just minutes away from everything the Rogue Valley has to offer. Whether you are visiting to taste award-winning wines, craft-brewed beers, experience outdoor concerts at the Britt - or all of the above - you will find you are right in the middle of the action.

16–23 Oct

$144 SGD per night